Twice Lucky - Cover

Twice Lucky

Copyright© 2003 by Joe J

Chapter 8

Time Travel Sex Story: Chapter 8 - If you knew then what you know now, how would you act?

Caution: This Time Travel Sex Story contains strong sexual content, including mt/ft   Ma/ft   mt/Fa   ft/ft   Fa/ft   Consensual   Romantic   BiSexual   Time Travel   DoOver   Incest   Brother   Sister   Safe Sex   Oral Sex   Anal Sex   Pregnancy  

It was the last week in August, and school would start next week. Helen took Jake and his sisters school shopping. Jake picked out the kind of nice clothes he wished his former family could have afforded for his first trip through high school. The girls excitedly picked tasteful outfits that fit their new self-images. They asked his opinion and seemed to want his advice. Of course, they also checked with Helen on each item and got her okay. He hated shopping but he enjoyed the fashion show his sisters put on. At one point his sisters talked their mom into trying on the same outfit they were both getting. All three came out of the dressing room in denim miniskirts and tight tops. Helen was already showing the results of her workouts. She looked more like an older sister than a mom. Jake whistled his appreciation and they fled back to the dressing rooms, laughing gaily. Helen bought the miniskirt for herself.

Jake’s new exercise regimen included Helen’s sessions after Debbie’s. He saved his upper body workout until he was with Helen. This meant that he could work out for a full hour and get to spend more time on each muscle group. Helen exercised with single-minded determination and really pushed herself. In two weeks, results were starting to show. She had lost five pounds and most of her tummy. She was thrilled. She was also happy that Charles had agreed to walk with her and nearly every evening they strolled off, hand in hand. Helen adopted the sundress uniform around the house and wore her hair down now. She looked vibrant and youthful. And Jake noticed that his father looked a lot happier. In the morning, a vibrant Helen, wearing a sexy little sundress, would kiss Charles soundly and he would leave for work dazed and smiling.


Jake spent Wednesday with Sara, Cindy, and Christopher at the beach. They had a great time, Sara made sure that Jake and Cindy had plenty of time by themselves. Cindy had on a demure one-piece but it couldn’t hide the beauty of her budding young body. Sara had on a modest but over-taxed two-piece that strained to hold her big breasts.

Jake and Cindy were lying side by side on their blanket watching Sara and little Chris.

Cindy leaned over and whispered in his ear, “Do you like playing with Sara’s big boobs?”

Jake looked at her, startled, “Why would you ask me that?”

“I know you and Sara are lovers, and I’m glad. I love you and I love it when you touch me; but I’m not ready to go all the way yet, so I’m happy that someone else I love is taking care of you. Besides, I saw them when she was putting on her bathing suit -- they look yummy. What do they feel like?”

Jake swatted her on the ass and said, “Why don’t you find out for yourself?”

Cindy yelped and surprised him by saying, “Maybe I will. After all, I go to a Catholic girls’ school and the only way we know anything about sex is from each other.”

When they got back to Sara’s, a tuckered-out Christopher went down for a nap. Jake had been thinking about what Cindy had said and decided to call her bluff. While she was in the bathroom, Jake pulled Sara aside and told her about his conversation with Cindy. At first Sara was alarmed that Cindy knew about Jake and herself but settled down when she realized Cindy was cool with it. Jake told her his scheme. With an excited grin, Sara agreed to it and headed to her bedroom.

When Cindy came out of the bathroom, Sara called her into the bedroom. As soon as Cindy was in the room, Sara handed her a bottle of aloe and said, “Can you put some of this on my back so I don’t burn?”

“Sure,” said Cindy.

Sara stripped off her top and lay down on the bed. Cindy started rubbing in the lotion, she looked up and saw Jake standing in the doorway. She stuck out her tongue at him.

“Roll over,” Cindy told Sara.

Sara rolled unto her back and Cindy rubbed lotion on her neck, shoulders, and arms. Then she smoothed the aloe onto the upper slopes of Sara’s breasts. Sara made a small noise as Cindy slid her hands downward before circling her breasts and capturing her nipples. Cindy slowly kneaded Sara’s tits for a minute or two then abruptly stopped.

“That should keep you from burning too badly. By the way, you have lovely breasts,” said Cindy as she capped the bottle, dropped it on the bed, and left the room.

Cindy joined Jake in the living room. Smiling smugly, she sat in his lap and kissed him. A blushing Sara joined them in a few minutes and they chatted until Christopher woke up from his nap. Sara drove to the Sorensons’ house and Jake walked Cindy to the door. Cindy gave him a hug and told him to ask Sara how she enjoyed the lotion. Sara drove Jake home. Jake went to his room, took a shower, and beat his hard-on into soft oblivion.

This was the week the women in his life seem to have decided to torment him. And the women in his house appeared to have coordinated their tormenting. Wednesday night at about ten, Angie came to his room to show him her new camisole and tap pants. The outfit was a dark blue that matched her eyes. The teens ended up on the bed. The camisole was up around her neck and her entire breast was in Jake’s mouth. She dry humped him until she came. For the second time that day Jake had to take matters into his own hands.

Thursday morning Jake was working out with Helen when they heard a large truck pull up outside. They exited the garage and found a large bucket loader on a trailer behind a dump truck. After gawking at the sweaty but gorgeous Helen for a second, the driver said he was there to start excavating for the pool. Helen and Jake walked him around the house where the pool had been staked out. He went back around and began to unload the earthmover. Helen and Jake finished their workout. Her thank-you kiss was hot and demanding. For the first time it seemed she was kissing him for her benefit instead of his. She had him hard in a second and, to his astonishment, she ground against him and moaned into his mouth. She finally broke the kiss and dashed into the house. Jake waited until the lump in his pants went down and followed her in.

His sisters were excited about the pool and called their dad to tell him about it. Jake showered and put on some jeans and a shirt. He sat at the table shoveling down a huge bowl of raisin bran. Helen and his sisters were sitting with him, picking at toast and grapefruit.

“Can someone give me a ride to the warehouse? I want to see Rafe.”

Angie said she would. After breakfast, Jake kissed Helen and Debbie while Angie grabbed the keys to the Falcon. Jake made a mental note to talk to his dad about upgrading the girls’ wheels. He would be getting his license in fewer than five months and the Falcon was distressingly plain. They headed for the TFA warehouse talking about the pool. Angie’s sundress had ridden up and Jake was marveling at how long her legs were. She caught him looking and pulled it up till he could almost see her panties.

“Like what you see, big boy?” she vamped.

“God, yes,” he replied. “It will be a lucky guy who gets them wrapped around him.”

She grabbed his hand and put it on her thigh. “I have decided that the first guy they wrap around will be you,” she said solemnly.

Jake stared at her for a second then slid his hand up and cupped her mound, “When the time is right, I would be honored.”

She gave him a million-watt smile and spread her legs for him. He played with her all the way to the store, keeping her close to the edge but not taking her over. When they pulled up to the warehouse no one was in sight, so he slipped his finger under the leg band of her panties and slid it into her steaming virgin slit. He used his thumb on her clit and she came explosively. Jake kissed her on the cheek, jumped from the car, straightened his hard-on, and strode toward the warehouse. It took Angie a few minutes to recover before she drove home, smiling blissfully.

Jake ran into Rafe at the loading dock door. Rafe was walking out with an attractive and petite black woman. Rafe shook Jake’s hand and introduced Jake to his wife Janet. The Robinsons were on their way to lunch. Jake was invited to join them. They all went to the diner that Rafe and Jake frequented.

“Remind me to dress better next time I dine with executives,” Jake joked, referring to Rafe’s white shirt and tie.

Rafe laughed, “I still can’t get used to dressing this way, but Jan insists and your dad sure approves.”

“So how is it going?” asked Jake. “Are you able to keep up with the volume moving in and out of the warehouse?”

“Mostly, but inventory control is a nightmare. Jan’s an accountant and came down this morning to see if we could come up with a better system,” replied Rafe.

Jake turned to Jan, “Did you come up with anything?”

Jan said, “I think so, although it will take some effort to put it in place.”

“Tell me about it,” said Jake.

Jan went over her idea of using punched tabulating machine cards to keep up with the store’s inventory. Cards could be made for each received item. The card would be affixed to the furniture or appliance while it was in the warehouse. The cards would be removed prior to delivery. The cards would be run through the tabulating machine and a print-out of what had left the warehouse could be prepared weekly to assist in reordering. Jake liked the idea. It would track inventory and tell them which products moved fastest. Jake asked how long it would take someone to put the system in place. Jan told him about two weeks. Jake went back to the warehouse with them and asked how long Jan was staying that afternoon. Rafe told him she was helping him set up a filing system and would be there all day. She only worked part-time.

Jake caught a ride with a delivery truck to the store. He went to his dad’s office and was surprised to see that he had a new secretary. He introduced himself to her and asked if his dad could see him. Her name was Gail Martin and she buzzed his dad. Charles told her to show Jake in. Charles was pleased to see Jake at the store. They shook hands and both sat down. After chatting about how well business was doing and Jake told his dad about his conversation with the Robinsons. Charles agreed a new system sounded good and also agreed they should hire Janet Robinson to start and run it. Charles called the warehouse and asked Rafe and Jan to come to the store. By four that afternoon Jan was the new inventory and sales data manager.

After the Robinsons left, Jake headed for the door. Hand on the knob, he turned back to his father.

“I think I better ask Miss Martin to go out with me before Mom gets suspicious of you two,” Jake said with a straight face.

Charles looked startled then, laughing, said, “Get out of here.”

Jake went to the outer office and struck up a conversation with Gail. In three minutes he had her giggling and blushing, in five he had her phone number and a promise for a date some time in the future. He hung around the store till five and caught a ride home with his dad. Charles wasn’t surprised when Jake said Miss Martin had agreed to a date.


That night it was Helen who knocked on his bedroom door. She was wearing a silk dressing gown that reached almost to the floor. Jake was reading at his desk, so she sat on the edge of the bed. Helen asked him about the new inventory ideas and jokingly thanked him for getting between Charles and Miss Martin. Then she stood up and started untying the sash on her robe.

“You forgot to check my progress this morning because of the pool guys,” Helen said.

She dropped her robe and stood straight and proud. She was wearing a white lacy bra and panty set. The bra plunged in the center and showed lots of cleavage, the panties were high cut and fit perfectly. Jake got up from his desk and walked around her appraisingly. She was firming up nicely, her tummy was flat and her waist more nipped-in. Her ass seemed to ride higher and rounder than before and her arms were more defined. At this rate she would catch up with Debbie in a few months. Jake stepped closer and ran his fingertips across her stomach then around to her ass. Helen shivered at his touch and goose bumps sprang up on her arms.

Jake walked behind her and slipped his arms around her. Helen put her hands on his and leaned her head back against his chest. He bent his head down to nibble her neck and she moved his hand up to her breasts. Then she unfastened the front clasp of her bra. His hands covered her mounds.

“Do you think they are firmer?” She whispered.

“Yes,” he whispered back.

His fingers circled her nipples and she moaned. She spun around and sought his lips hungrily. He pushed her back onto the bed and fastened his lips to her hard rubbery nipple. Helen grabbed his hair and pulled his face against her breast whimpering softly. Jake had just gotten his hand on the front of her panties when she pushed his head from her breast and sat up.

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